Research Department of Chemistry, Nehru Memorial College (Affiliated Bharathidasan University), Puthanampatti, Tamilnadu, India.
Department of Botany and Microbiology, College of Science, King Saudi University, Riyadh, Saudi Arabia.
PLoS One. 2024 Sep 19;19(9):e0298232. doi: 10.1371/journal.pone.0298232. eCollection 2024.
The objective of this study was to develop pyrazolidine-3,5-dione derivatives with potential as environmentally friendly pesticides for pest control, specifically focusing on their efficacy as larvicidal agents. A novel one-pot synthesis of multicomponent pyrazolidine-3,5-dione derivatives (1a-m) was accomplished via the grindstone method using Cu(II)tyrosinase enzyme as a catalyst under mild reaction conditions, yielding 84%-96%. The synthesised derivatives (1a-m) were characterized using various spectroscopic methods (mass spectrometry, elemental analysis, FT-IR, and 1H and 13C NMR). NMR characterisation using DMSO-d6 as a solvent. The larvicidal and antifeedant activities of the synthesised compounds were screened and in silico computational studies were performed. The larvicidal activity against Culex quinquefasciatus and antifeedant activity against Oreochromis mossambicus were evaluated. Among the synthesised compounds, compound 1c demonstrated superior efficacy (LD50: 9.7 μg/mL) against C. quinquefasciatus compared to permethrin (LD50: 17.1 μg/mL). Regarding antifeedant activity, compounds 1a, 1e, 1f, 1j, and 1k exhibited 100% mortality at 100 μg/mL. Molecular docking analysis was performed to assess the binding capacity of a mosquito odorant-binding protein (3OGN) from Culex quinquefasciatus to compound 1c. The results revealed that compound 1c had a docking score of -10.4 kcal/mol, surpassing that of standard permethrin (-9.5 kcal/mol). Furthermore, DFT calculations were conducted to acquire theoretical data aligned with the experimental FT-IR results. According to experimental research, compound 1c demonstrates promising larvicidal activity against mosquito larvae of C. quinquefasciatus.
本研究旨在开发具有环境友好型杀虫剂潜力的吡唑烷-3,5-二酮衍生物，特别是将其作为杀幼虫剂的功效作为研究重点。通过使用 Cu(II)酪氨酸酶作为催化剂，采用磨石法在温和的反应条件下，以高收率（84%-96%）完成了新型一锅法合成多组分吡唑烷-3,5-二酮衍生物（1a-m）。采用各种光谱方法（质谱、元素分析、FT-IR 和 1H 和 13C NMR）对合成的衍生物（1a-m）进行了表征。使用 DMSO-d6 作为溶剂进行 NMR 表征。对合成化合物进行了杀虫和拒食活性筛选，并进行了计算机模拟研究。评估了对库蚊（Culex quinquefasciatus）的杀虫活性和对奥利亚罗非鱼（Oreochromis mossambicus）的拒食活性。在所合成的化合物中，化合物 1c 对库蚊（LD50：9.7 μg/mL）的杀虫活性优于氯菊酯（LD50：17.1 μg/mL）。在拒食活性方面，化合物 1a、1e、1f、1j 和 1k 在 100 μg/mL 时的死亡率均达到 100%。进行了分子对接分析，以评估 3OGN（来自库蚊的一种蚊子气味结合蛋白）与化合物 1c 的结合能力。结果表明，化合物 1c 的对接得分为-10.4 kcal/mol，超过了标准氯菊酯（-9.5 kcal/mol）。此外，还进行了 DFT 计算，以获得与实验 FT-IR 结果相符的理论数据。根据实验研究，化合物 1c 对库蚊幼虫表现出有希望的杀虫活性。
